ChemicalBook CAS DataBase List 4199-10-4

4199-10-4

Name	(S)-(-)-PROPRANOLOL HYDROCHLORIDE
CAS	4199-10-4
EINECS(EC#)	224-096-0
Molecular Formula	C16H22ClNO2
MDL Number	MFCD00064547
Molecular Weight	295.8
MOL File	4199-10-4.mol

Synonyms

2S-(-)-PROPANOLOL HYDROCHLORIDE (S)-(-)-1-[(1-METHYLETHYL)AMINO]-3-(1-NAPHTHALENYLOXY)-2-PROPANOL HYDROCHLORIDE (S)-1-ISOPROPYLAMINO-3-(1-NAPHTHYLOXY)-2-PROPANOL HYDROCHLORIDE S-(-)-PROPANOLOL HCL S(-)-PROPRANOLOL HCL (S)-(-)-PROPRANOLOL HYDROCHLORIDE (S)-PROPRANOLOL HYDROCHLORIDE (S)-[2-hydroxy-3-(naphthyloxy)propyl]isopropylammonium chloride 2-Propanol, 1-(1-methylethyl)amino-3-(1-naphthalenyloxy)-, hydrochloride, (2S)- 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride, (2S)-(9CI) 2-Propanol, 1-[(1-methylethyl)amino]-3-(1-naphthalenyloxy)-, hydrochloride, (S)- L-(-)-Propranolol hydrochloride l-Propranolol chlorhydrate l-Propranolol hydrochloride S-(-)-1-Isopropylamino-3-(1-naphthoxy)-2-propanol hydrochloride S-PROPANOLOL (S)-1-(isopropylamino)-3-(naphthalen-1-yloxy)propan-2-ol hydrochloride (S)-(-)-1-(1-Methylethylamino)-3-naphthalen-1-yloxy-propan-2-ol hydrochloride (2S)-1-(1-Naphtyloxy)-3-(isopropylamino)-2-propanol·hydrochloric acid

Chemical Properties

Melting point	193-195 °C(lit.)
storage temp.	2-8°C
solubility	ethanol: 10 mg/mL
form	powder
color	White to off-white
Optical Rotation	[α]25/D 25.5°, c = 1.0 in ethanol(lit.)
Water Solubility	Soluble to 100 mM in water
BRN	3574966
InChI	1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1
InChIKey	ZMRUPTIKESYGQW-UQKRIMTDSA-N
SMILES	Cl[H].CC(C)NC[C@H](O)COc1cccc2ccccc12
CAS DataBase Reference	4199-10-4(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302+H312+H332
Precautionary statements	P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Hazard Codes	Xn
Risk Statements	R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . less more
Safety Statements	S36:Wear suitable protective clothing . less more
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral

Hazard Information

Description

(S)-(-)-Propranolol is the active enantiomer of propranolol, a β-adrenergic receptor antagonist with log K_d values of -8.16, -9.08, and -6.93 for β₁, β₂, and β₃, respectively. It is also a non-specific serotonin receptor antagonist. Propanolol was one of the first β-adrenergic receptor blockers to be widely used in clinical practice for the treatment of hypertension, angina pectoris, and cardiac ischemia.

Chemical Properties

(S)-(-)-1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol hydrochloride

Uses

active enantiomer, 5-HT1 receptor antagonist

Uses

Antihypertensor;Beta-adrenergic blocking agent

Uses

The S-enantiomer of Propranolol (P831800). β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

Biological Activity

More active enantiomer of the β -adrenoceptor antagonist propranolol ((RS)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol hydrochloride ).

Biochem/physiol Actions

(S)-(?)-Propranolol hydrochloride is biologically active enantiomer. It acts as β1 receptor antagonist in thalamocortical neurons. (S)-(?)-Propranolol hydrochloride elicits its inhibitory function on the β1 adrenoceptor in trigeminovascular pain pathway and serves as a preventive medicine in migraine.

storage

Store at RT

Purification Methods

The (+)-salt is the active isomer which blocks isoprenaline tachycardia and is a -adrenergic blocker. [Leclerc et al. Trends Pharmacol Sci 2 18 1981, Howe & Shanks Nature 210 1336 1966.]

References

[1] D W COSTAIN A R G. beta-Adrenoceptor antagonists inhibit the behavioural responses of rats to increased brain 5-hydroxytryptamine.[J]. British Journal of Pharmacology, 1978, 64 2: 193-200. DOI: 10.1111/j.1476-5381.1978.tb17289.x

Spectrum Detail

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